"When I was on Islay (which eveyone there pronounced 'eye-lah')"
Because that's the name of the island.
"Caol Ila was universally pronounced 'cull ee-lah' and not like the island itself (and the linked video)."
Caol Ila is a Gaelic, not an English name. Ile (that's I-L-E, if the font isn't distinguishing between the first and second letters, pronounced more or less 'ee-lah') is the name of the island in Gaelic. 'Ila' is an alternative spelling of it. Here's a Gaelic map of Scotland (= Alba) in case anyone's interested.
'Islay' is a fairly spurious anglicised spelling invented by some English speaker who thought there ought to be an 's' in it - well, it's an iSland, isn't it? - but the 'y' on the end is in line with the Scandinavian-origin '-ay' and '-ey' endings you see elsewhere in the Hebrides (e.g. Eriskay, Berneray) and the Northern Isles (e.g. Sanday in the Orkneys, Whalsay in the Shetlands). The Gaelic renderings of these placename elements can be all sorts of things - '-aigh' is a common one - but since the Northern Isles was never a Gaelic-speaking area, they remained with '-ay'/'-ey'. However, Islay was under Scandinavian rule for quite a long time, so it has a good reason for being spelled '-ay'. Like Colonsay and Scalpay, which are close by, but not like Jura and Gigha, which are other neighbouring islands which have lost their 'y'.
La-FROYK, if you don't mind.
No-one's mentioned Bowmore or Port Charlotte. I wonder why? Too easy to say, probably.
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